Covalent sequestration of the nitrogen mustard mechlorethamine by metallothionein

Drug Metabolism and Disposition

Volumn 26, Issue 9, 1998, Pages 921-926

  Antoine, Miquel ^b   Fabris, Daniele ^b   Fenselau, Catherine ^a  

^a Bldg 142   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

CHLORMETHINE DERIVATIVE; METALLOTHIONEIN;

ALKYLATION; ANIMAL TISSUE; ARTICLE; COVALENT BOND; CROSS LINKING; DRUG BINDING; DRUG DISTRIBUTION; DRUG INACTIVATION; GENE OVEREXPRESSION; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; RABBIT;

ALKYLATING AGENTS; ALKYLATION; ANIMALS; CARBOXYPEPTIDASES; COMPUTER SIMULATION; HYDROLYSIS; MECHLORETHAMINE; METALLOTHIONEIN; MOLECULAR WEIGHT; PROTEIN BINDING; RABBITS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; TRYPSIN;

EID: 0031706609     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. 7]metallothionein-2a in aqueous solution determined by nuclear magnetic resonance. J Mol Biol 201:637-657.
2. Basu A and Lazo JS (1990) A hypothesis regarding the protective role of metallothioneins against the toxicity of DNA-interactive anticancer drugs. Toxicol Lett 50:123-135.
3. Biemann K (1988) Contributions of mass spectrometry to peptide and protein structure. Biomed Environ Mass Spectrom 16:99-111.
4. Brouwer M (1996) Role of metallothionein in intracellular metal metabolism and in activation of copper-and zinc-dependent proteins. Adv Inorg Biochem 11:235-260.
5. Cagen SZ and Klaassen CD (1980) Binding of glutathione-depleting agents to metallothionein. Toxicol Appl Pharmacol 54:229-237.
6. Colvin M and Chabner BA (1990) Alkylating agents, in Cancer Chemotherapy: Principles and Practice (Chabner BA and Collins JM eds) pp 276-313, J. B. Lippincott, Philadelphia.
7. Cotter RJ (1994) Analysis of peptides and proteins using time-of-flight mass spectrometry, in Therapeutic Aspects and Analytical Methods in Cancer Research (Constantin E ed) pp 85-95, Amudes, Strasbourg.
8. Cummings J, MacLellan A, Smyth JF and Farmer PB (1991) Determination of reactive nitrogen mustard anticancer drugs in plasma by high-performance liquid chromatography using derivatization. Anal Chem 63:1514-1519.
9. Doz F, Roosen N and Rosenblum ML (1993) Metallothionein and anticancer agents: the role of metallothionein in cancer chemotherapy. J Neurooncol 17:123-129.
10. Dumam DM and Palmiter RD (1981) Transcriptional regulation of the mouse metallothionein-I gene by heavy metals. J Biol Chem 256:5712-5716.
11. Endresen L, Bakka A and Rugstad HE (1983) Increased resistance to chlorambucil in cultured cells with a high concentration of cytoplasmic metallothionein. Cancer Res 43:2918-2926.
12. Fenselau C (1997) Electrospray mass spectrometric characterization of adducts between therapeutic agents and proteins. Annu Rep Med Chem 32:269-276.
13. Fowle DA and Stillman MJ (1997) Comparison of the structures of the metal-thiolate binding site in Zn(II)-, Cd(II)-, and Hg(II)-metallothioneins using molecular modeling techniques. J Biomol Struct Dyn 14:393-406.
14. Hamer DH (1986) Metallothionein. Annu Rev Biochem 55:913-951.
15. Hartley JA, Bingham JP and Souhami RL (1992) DNA sequence selectivity of guanine-N7 alkylation by nitrogen mustards is preserved in intact cells. Nucleic Acids Res 20:3175-3178.
16. Hathout Y, Ellis T, Fabris D and Fenselau C (1996) Cross-linking of human placenta π class glutathione S-transferase dimer by chlorambucil. Chem Res Toxicol 9:1044-1049.
17. Hopkins PB, Millard JT, Woo J, Weidner MF, Kirchner JJ, Sigurdsson ST and Raucher S (1991) Sequence preferences of DNA interstrand cross-linking agents: importance of minimal DNA structural reorganization in the cross-linking reactions of mechlorethamine, cisplatin, and mitomycin C. Tetrahedron 47:2475-2489.
18. Hunziker PE (1991) Cysteine modification of metallothionein. Methods Enzymol 205:399-400.
19. Kagi JHR (1991) Overview of metallothionein. Methods Enzymol 205:613-626.
20. Kagi JHR (1993) Evolution, structure and chemical activity of class I metallothioneins: an overview, in Metallothionein III (Suzuki KT, Imura N and Kimura M eds) pp 29-55, Birkhauser Verlag, Basel, Switzerland.
21. Kagi JHR and Kojima Y (1987) Chemistry and biochemistry of metallothionein. Experientia (Basel) 52(Suppl):25-61.
22. Karin M and Herschman HR (1979) Synthesis in HeLa cell cultures. Science (Washington DC) 204:176-177.
23. Kelley SL, Basu A, Teicher BA, Hacker MP, Hamer DH and Lazo JS (1988) Overexpression of metallothionein confers resistance to anticancer drugs. Science (Washington DC) 241:1813-1815.
24. Kelly EJ, Quaife CJ, Froelick GJ and Palmiter RD (1996) Metallothionein I and II protect against zinc deficiency and zinc toxicity in mice. J Nutr 126:1782-1790.
25. Kotsonis FN and Klaassen CD (1979) Increase in hepatic metallothionein in rats treated with alkylating agents. Toxicol Appl Pharmacol 51:19-27.
26. Li T-Y, Kraker AJ, Shaw CF III and Petering DH (1980) Ligand substitution reactions of metallothioneins with EDTA and apo-carbonic anhydrase. Proc Natl Acad Sci USA 77:6334-6338.
27. Margoshes M and Vallee BL (1957) A cadmium protein from equine kidney cortex. J Am Chem Soc 79:4813-4814.
28. Messerle BA, Bos M, Schaffer A, Vasak M, Kagi JHR and Wuthrich K (1990) Amide proton exchange in human metallothionein-2 measured by nuclear magnetic resonance spectroscopy. J Mol Biol 214:781-786.
29. Oh SH, Deagen JT, Whanger PD and Weswig PH (1978) Biological function of metallothionein. V. Its induction in rats by various stresses. Am J Physiol 234:E282-E285.
30. Osbome MR, Wilman DE and Lawley PD (1995) Alkylation of DNA by the nitrogen mustard bis(2-chloroethyl)methylamine. Chem Res Toxicol 8:316-320.
31. Otvos JD and Armitage IM (1980) Structure of the metal clusters in rabbit liver metallothionein. Proc Natl Acad Sci USA 77:7094-7098.
32. Richards MP and Cousins RJ (1976) Metallothionein and its relationship to the metabolism of dietary zinc in rats. J Nutr 106:1591-1599.
33. Rink SM and Hopkins PB (1995) A mechlorethamine-induced DNA interstrand cross-link bends duplex DNA. Biochemistry 34:1439-1445.
34. Robbins AH, McRee DE, Williamson M, Collett SA, Xuong NH, Furey WF, Wang BC and Stout CD (1991) Refined crystal structure of Cd,Zn metallothionein at 20 Å resolution. J Mol Biol 221:1269-1293.
35. Skipper PL (1996) Influence of tertiary structure on nucleophilic substitution reactions of proteins. Chem Res Toxicol 9:918-923.
36. Vallee BL (1995) The function of metallothionein. Neurochem Int 27:23-33.
37. Vasak M, Worgotter E, Wagner G, Kagi JHR and Wuthrich K (1987) Metal co-ordination in rat liver metallothionein-2 prepared with or without reconstitution of the metal clusters, and comparison with rabbit liver metallothionein-2. J Mol Biol 196:711-719.
38. Yergey J, Heller D, Hansen G, Colter RJ and Fenselau C (1983) Isotopic distributions in mass spectra of large molecules. Anal Chem 55:353-356.
39. Yu X, Wu Z and Fenselau C (1995) Covalent sequestration of melphalan by metallothionein and selective alkylation of cysteines. Biochemistry 34:3377-3385.
40. Zaia J, Jiang L, Han MS, Tabb JR, Wu Z, Fabris D and Fenselau C (1996) A binding site for chlorambucil on metallothionein. Biochemistry 35:2830-2835.